Reduction of [m.3.3]Propellane Ketones in Solution Aggregates

Anand Natrajan, Chaim N. Sukenik

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The reduction of [m.3.3]propellane diones and ketols has been studied in water containing cationic, anionic, and zwitterionic surfactants. From the rate and stereochemistry of the reductions done in these media, the binding of neutral substrates and ionic reagents to surfactant aggregates has been probed. Surface interactions of these variously charged aggregates have been studied, and the behavior of aggregates with like charge but different structure (cationic aqueous micelles, vesicles, and reverse micelles) has been compared. A picture of charge distribution at the surface of amine oxide zwitterionic micelles has emerged. The oriented propellane binding (polymethylene ring aligned with surfactant tails and fused five-membered rings tangential to the aggregate surface) first proposed for propellanes bound to cationic micelles has been confirmed and extended to cationic vesicles and to amine oxide micelles.

Original languageEnglish
Pages (from-to)3559-3563
Number of pages5
JournalJournal of Organic Chemistry
Volume53
Issue number15
DOIs
StatePublished - 1 Feb 1988
Externally publishedYes

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